Diamond Head Homes for Sale

Welcome to Diamond Head, a picturesque neighborhood nestled on the southeastern coast of Oahu, Hawaii. Renowned for its iconic volcanic crater and stunning ocean views, this vibrant community offers a unique blend of natural beauty and urban convenience. With its proximity to the bustling city of Honolulu, residents enjoy the best of both worlds—serenity and accessibility.

Diamond Head is not just a feast for the eyes; it's a haven for outdoor enthusiasts. The famous Diamond Head State Monument invites locals and visitors alike to hike its scenic trails, rewarding adventurers with panoramic vistas of the Pacific Ocean and the lush landscape below. The neighborhood's pristine beaches, such as Kaimana Beach and the renowned Waikiki, provide ample opportunities for sunbathing, swimming, and surfing.

When it comes to real estate, Diamond Head boasts a diverse array of homes for sale, from charming single-family residences to luxurious oceanfront condos. Many properties feature breathtaking views, spacious layouts, and lush tropical gardens, making them an ideal choice for families, retirees, and anyone looking to embrace the Hawaiian lifestyle. Imagine waking up to the sound of waves crashing and enjoying your morning coffee on a lanai overlooking the majestic Diamond Head crater.

With a strong sense of community and a laid-back atmosphere, Diamond Head is more than just a place to live—it's a lifestyle. Whether you're looking to invest in a vacation home or seeking a permanent residence, the homes for sale in this enchanting neighborhood offer a unique opportunity to experience the beauty of island living. Discover your slice of paradise in Diamond Head today!

Newest Diamond Head Homes for Sale

$2,275,000

5 Beds ⋅ 4 Baths ⋅ 202615526 MLS ⋅ FS - Fee Simple Tenure ⋅ 0 DOM

MUST SEE! This stunning Kapahulu residence offers a fresh, modern and cohesive living environment with thoughtful updates throughout - providing the peace of mind and feel of a truly renewed home. With an additional living space downstairs, this flexible two-story floor plan offers excellent versatility for multigenerational living, guests or a variety of lifestyle needs. Enjoy a newly landscaped yard, enhanced with exterior lighting and irrigation, creating a beautiful and functional outdoor space for relaxing or entertaining. Generous parking, including a covered carport and additional on-site parking. Walk to Safeway, Starbucks, dining and everyday conveniences with Waikiki, Diamond Head and beaches just minutes away. A rare opportunity to own a truly move-in-ready home in one of Honolulu's most convenient and sought after neighborhoods.

3237 Olu Street, Honolulu

$2,395,000

5 Beds ⋅ 3 Baths ⋅ 202615817 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 DOM

Built in 2022 and ideally positioned on lower Sierra Dr., this modern 5-bedroom, 3-bath home captures unobstructed, sweeping ocean, coastline & city views from this perimeter lot. Thoughtfully designed to take advantage of the views and natural light, the home offers a flexible floor plan well suited for everyday living, entertaining, guests, or extended family. Entry level offers large glass sliding doors opening to a large lanai off the kitchen and living areas and a bedroom with full bath. Lower level features a second open living room with the additional 4 bedrooms, 2 baths, laundry and 2 additional lanai's, plus a landscaped Living wall off the bedroom glass sliding doors. High ceilings, sprinklers, ceiling fans and privacy make this home feel like it's perched on the edge of the world. Enjoy the benefits of newer construction in one of Honolulu's most established hillside neighborhoods, just mins from Kaimuki, Waialae Ave, dining, shopping, schools, and freeway access. The property includes a 2-car carport plus 2 additional guest parking stalls—a valuable convenience in the area. Driveway is shared. All decks repainted.

3616 Sierra Drive, Honolulu

$2,050,000

6 Beds ⋅ 3 Baths ⋅ 202615523 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 DOM

Views, convenience and privacy! Minutes from Kahala Mall, schools, medical clinics and H-1 freeway access, this lower Waialae Nui Ridge home offers views of the sparkling Kahala coastline, Diamond Head and Waikiki skyline. Flexible SINGLE LEVEL floorplan includes 6 bedrooms, 3 bathrooms and a spacious family room. Enjoy mornings and unwind in the evenings on the covered view lanai. A variety of mature fruit trees enhance the yard with room to garden. Wonderful corner location with driveway on Uhi Place.

1688 Halekoa Drive, Honolulu

$1,448,000

3 Beds ⋅ 2 Baths ⋅ 202615153 MLS ⋅ FS - Fee Simple Tenure ⋅ 4 DOM

A Timeless and Classic Home … Perched above Center Street in sought-after Wilhelmina, this beautifully updated vintage home blends timeless character with thoughtful modern enhancements. Originally built in 1928 and extensively renovated in 2015, the residence retains its distinctive charm while offering comfortable contemporary living. High ceilings, abundant windows, and beautiful wood flooring create a warm, inviting atmosphere filled with natural light. The flexible lower-level 3rd bedroom/studio space is a feature incorporating natural boulders into its design and offering its own wetbar and beautifully finished on-suite bath all add an elevated touch. On the main level, step outside to an expansive deck ideal for morning coffee, sunset gatherings, and entertaining which you’ll enjoy while taking in views from Palolo Valley, the city and ocean all adding to its appeal. Conveniently located near the entertainment of Kaimuki's dining, shopping and easy access to the freeway.

1439 Center Street, Honolulu

$1,400,000

3 Beds ⋅ 2 Baths ⋅ 202615578 MLS ⋅ FS - Fee Simple Tenure ⋅ 5 DOM ⋅ Kalani Iki Estates BLDG.

Tucked away in a cool, quiet & peaceful neighborhood, Kalani Iki Estates feels uniquely special as you arrive through the lush tree-lined community. This bright, modern 3-bedroom, 2-bath split-level home has been exceptionally maintained & thoughtfully updated. Soaring high ceilings & wrap-around floor-to-ceiling windows welcome you home to a contemporary floor plan, natural light & garden views throughout. Features & upgrades include a re-imagined kitchen with new quartz counter-tops & updated appliances, a dedicated dining space, luxury vinyl flooring, all-new windows & doors throughout, upgraded lighting, roller & zebra shades, two split A/C units & more. Three bedrooms are positioned on the upper-level for added privacy, plus a walk-in storage & walk-in laundry room. This home includes two covered parking stalls. Furnishings available for purchase to make this a turn-key package. Kalani Iki Estates includes landscaping & trash service, an on-site swimming pool, large covered entertainment space & a newly refurbished pickleball court. Minutes to Kahala, Hawaii Kai, urban Honolulu & beyond, this exceptional home in a truly special location is one you won't want to miss.

1500 Kalaniiki Street Unit 13, Honolulu

$1,275,000

3 Beds ⋅ 2 Baths ⋅ 202609335 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM

Vintage 1940's bungalow located in the super convenient Kapahulu area at the base of Diamond Head Crater. This charming home with many original features, that made it so cute, are intact and has been meticulously maintained throughout the years. Kitchen and bathrooms have been remodeled to todays standards... New fixtures, new appliances - including a gas range, AC's and ceiling fans in each room, new cabinetry, LVP flooring, fresh paint, lighting etc. makes this a perfect move-in ready home. Nicely landscaped exterior with full grassy areas, large mango tree for cool shade, fully fenced and gated yard, multiple tandem car parking with a laundry / storage room behind the carport are all features that make this a great property! There is a large concrete patio off the laundry room... possible extension for a future home office or additional bedroom? Definitely a classically adorable, move-in ready property on the outskirts of Waikiki!

3327 Catherine Street, Honolulu

$5,200,000

4 Beds ⋅ 5 Baths ⋅ 202615535 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM

Your own Kahala retreat on the secluded Ahina Street awaits with this expansive single level, 4 bedroom, 4.5 bath unit with pool. Rooms are split into 2 wings for privacy. Call your agent and take a look!

559 Ahina Street, Honolulu

$1,750,000

5 Beds ⋅ 3 Baths ⋅ 202615465 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM

Built in 2016 and upgraded in 2026, this 5-bedroom, 3-bath home offers a flexible two-story layout, a spacious fenced grassy yard and parking for up to six vehicles, a combination that is increasingly difficult to find in town. The upper level features 3 bedrooms and 2 full baths, while the lower level offers 2 bedrooms and 1 full bath. Separate entrances provide added privacy and flexibility for a large or multigenerational household, extended family, guests, or potential rental income. Recent upgrades include brand-new luxury vinyl flooring throughout, fresh interior paint, new window AC units and split AC systems. Outside, the large fenced yard provides usable space for pets, entertaining or simply enjoying more outdoor space at home. Ample "off-street" parking accommodates up to six vehicles, and additional storage closets in the garage provide valuable space for tools, equipment and everyday storage. Conveniently located in Palolo with quick access to Kaimuki and Waialae Avenue, UH Manoa, Kahala and Waikiki, along with nearby shopping, dining, schools and freeway access. This rare home offers many options for buyers who need more space and flexibility.

1633 10th Avenue Unit Apt B, Honolulu

$1,295,000

5 Beds ⋅ 3 Baths ⋅ 202614648 MLS ⋅ FS - Fee Simple Tenure ⋅ 8 DOM

“Own an original”: The original owner of these beautiful, classic homes in Palolo valley is ready for the next generation of owners, investors, or developers to call this place home. Nestled on the mauka (mountain) side of 10th Avenue, you feel like you are in a special retreat, away from the hustle and bustle of the urban core, yet only 1 mile from Wai’alae Ave in the vibrant neighborhood community of Kaimuki - close to locally owned restaurants, retail shops and bus lines. Two separately metered (water, sewer and electrical) single family homes with an enclosed 2 car garage on 10th Ave. Main home on 10th Ave is a 3 bd / 1.5 bath with an unfinished basement for extra storage or remodel potential and covered lanai. Upper home 2 bd / 1 ba with a spacious, terraced backyard of property with even more potential to extend or build; buyer to do their own due diligence regarding permitting and capacity to build. Conveniently located across from Palolo Elementary, two blocks from Honolulu Fire Dept Station and 4 blocks away from Palolo Community Center with swimming pool, basketball courts and baseball field.

2077 10th Avenue, Honolulu

$1,399,000

4 Beds ⋅ 3 Baths ⋅ 202614936 MLS ⋅ FS - Fee Simple Tenure ⋅ 8 DOM

Rare Opportunity! This unique property features two separate dwellings on a spacious 4,500 sq. ft. lot, offering exceptional flexibility for extended family, guests, or rental income potential. The back residence (approx. 1,008 sq. ft.) includes a versatile 2-bed/2-bath layout, while the front residence (approx. 528 sq. ft.) includes 2-bed/1-bath. Adding further value is an owned photovoltaic system with 25 panels, offering energy efficiency and potential long-term utility savings. Ideally located in the desirable Kapahulu neighborhood, just minutes from Diamond Head, Waikiki and world-class shopping, dining, beaches, and more. Don't miss out on this exceptional opportunity!

3473 Winam Avenue, Honolulu

$1,825,000

5 Beds ⋅ 3 Baths ⋅ 202614839 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM

Most homes trade elevation for the view—climb higher, live farther from everything. This Halekoa Drive home rewrites that story: nearly 180 degrees of open ocean and Diamond Head from every level, perched low enough to keep daily life close. Four bedrooms sit upstairs; below, a detached rental unit with its own entrance, bath, and wet bar gives you a flexible lower level - an income offset, a guest suite, or extra room for your Ohana. Sixteen owned solar panels and solar hot water run on net metering, putting the energy math in your favor. A neighborhood park sits just a few blocks off, and the address lands in some of Honolulu's most sought-after public school districts. This house is built for the buyer who wants the unobstructed views without the climb. The home has been tastefully maintained with contemporary flooring, spacious bedrooms, and an EV equipped garage you can pull into after a long day at the beach. You can count on one hand how many homes on the hill like this come to market. Don't miss your chance to stand in this space and feel the tranquility it holds. Call your favorite realtor today for a private showing, and welcome home.

1492 Halekoa Drive, Honolulu

$1,050,000

3 Beds ⋅ 2 Baths ⋅ 202614650 MLS ⋅ FS - Fee Simple Tenure ⋅ 11 DOM

Welcome to this hidden gem, 1878A Mahana Street. Tucked away down a flag lot in the heart of Palolo Valley, this well-maintained, single level, 3-bed, 2-bath home is ready for its next chapter. Whether you're looking to move right in or bring your vision to life, the possibilities are endless. The property enjoys a quiet retreat from the street allowing you to curate your own private oasis while still remaining conveniently close to everything Honolulu has to offer. Inside, the thoughtfully designed 1,445 sq. ft. floor plan features 2 living spaces, perfect for entertaining and hosting your favorite people. A natural cross breeze and tons of natural light move through the home, creating a comfortable living environment year-round. The flexible indoor-outdoor space is great for gardening, grilling, or simply relaxing after a long day. With 2 carports and a driveway, this home can hold up to 4 cars with additional parking on the street. Opportunities like this are becoming increasingly rare, especially in a desirable & convenient area like Palolo.

1878-A Mahana Street, Honolulu

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Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.